Sodium Iodide → 4-(4-(2-(4-(3-Trifluoromethylphenyl)piperazinyl)ethyl)phenyl)-2-methylthiazole

HRID 329404

Reaction equation

HRID 329404 reaction equation
Br.Cl[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([CH3:16])[S:14][CH:15]=2)=[CH:7][CH:6]=1.Cl.[F:18][C:19]([F:33])([F:32])[C:20]1[CH:21]=[C:22]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:23]=[CH:24][CH:25]=1.C(N(C(C)C)CC)(C)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>CC(CC(C)C)=O>[F:33][C:19]([F:18])([F:32])[C:20]1[CH:21]=[C:22]([N:26]2[CH2:31][CH2:30][N:29]([CH2:3][CH2:4][C:5]3[CH:10]=[CH:9][C:8]([C:11]4[N:12]=[C:13]([CH3:16])[S:14][CH:15]=4)=[CH:7][CH:6]=3)[CH2:28][CH2:27]2)[CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 3084246TFMPP hydrochlorideHCID 147269914-(4-(2-Chloroethyl)phenyl)-2-methylthiazole hydrobromide

Product 1

HCID 147270144-(4-(2-(4-(3-Trifluoromethylphenyl)piperazinyl)ethyl)phenyl)-2-methylthiazole

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To a 125 ml round-bottomed flask equipped with condenser and N2 inlet were added 2.39 g (7.5 mmol) of 4-(4-(2-chloroethyl)phenyl)-2-methylthiazole hydrobromide, 2.0 g (7.5 mmol) of N-(3-trifluoromethylphenyl)piperazine hydrochloride, 2.62 ml (15.0 mmol) of diisopropylethylamine, 1.59 g (15.0 mmol) of sodium carbonate, 5 mg of sodium iodide, and 50 ml of methylisobutylketone. The reaction was heated at reflux for 4.5 days, filtered hot to remove inorganic material, cooled, and the precipitate filtered and washed with ether and ethyl acetate. The solid was taken up in methylene chloride, hydrochloride gas bubbled through to precipitate the salt, and the resulting solid filtered, washed with methylene chloride, and dried to give a solid, m.p. 170°-175° C., 1.93 g (51%).

Workup

  1. customTo a 125 ml round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 4.5 days
  4. filtrationfiltered hot
  5. customto remove inorganic material
  6. temperaturecooled
  7. filtrationthe precipitate filtered
  8. washwashed with ether and ethyl acetate
  9. custombubbled through
  10. customto precipitate the salt
  11. filtrationthe resulting solid filtered
  12. washwashed with methylene chloride
  13. customdried
  14. customto give a solid, m.p. 170°-175° C., 1.93 g (51%)

Sources & evidence

ORD record
ord-657c9b01e2664e808756328b3d3ef8e0
Source dataset
uspto-grants-1990_01
Patent number
US04891375

Linked notes

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